title: Cyclodehydration of N-(aminoalkyl)benzamides under mild conditions with a Hendrickson reagent analogue.
abstract: Methods for the cyclodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducts.
authors.affiliation: School of Biomolecular and Physical Sciences, Griffith University, Nathan, QLD 4111, Australia.
authors.forename: Wendy A
authors.initials: WA
authors.lastname: Loughlin
authors.forename: Ian D
authors.initials: ID
authors.lastname: Jenkins
authors.forename: Maria J
authors.initials: MJ
authors.lastname: Petersson
mesh_terms: D000578:Amidines / Q000138:chemical synthesis* / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D003500:Cyclization; D003681:Dehydration; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*
chemical_list: D000578:Amidines; D000812:Anhydrides; D001549:Benzamides; D009943:Organophosphorus Compounds